▲The Queen of Pop won one of the first prizes of her career at the American Music Awards in 1985.

▲The now-famous actress accompanied her father, actor Jon Voight and star of 'Runaway Train,' for her red carpet debut in 1986.

▲While her 1998 appearance for the premiere of 'The Horse Whisperer' wasn't her first, it was what launched her towards success in Hollywood.

▲Pictured in 1993, at the age of 19, DiCaprio starred in 'What's Eating Gilbert Grape,' and was also nominated for the Oscar for Best Supporting Actor.

▲The actress first appeared at the Oscars in 1996, at the age of 20, when she was nominated for Best Supporting Actress for her role in 'Sense and Sensibility.' The hit film 'Titanic' would come out the following year.

▲The actress was eight years old in 1982, when the film 'E.T. the Extra-Terrestrial,' directed by Steven Spielberg, won several Oscars. Her little dress was reportedly made by her mother!

▲The actress walked the 1991 red carpet, aged 15, for the premiere of 'Man in the Moon.'

▲Pictured in 1991, the actor accompanied his girlfriend at the time, Juliette Lewis, who was nominated for the Oscar for Best Supporting Actress for her role in 'Cape Fear.'

▲Seemingly the Hollywood power couple of the '90s, the young actors fell in love on the set of 1990's 'Flatliners' and walked the red carpet at the Oscars together that same year.

▲In 1996, years before winning Best Actress for her role in 'Monster's Ball,' Halle Berry dazzled on the red carpet.

▲The South African actress was already stunning, but relatively unknown when she attended the 1996 premiere of 'Two Days in the Valley.'

▲The super young George Clooney made his 1986 red carpet debut at an event for Amnesty International.

▲In 1990, the same year their film 'Edward Scissorhands' was released, the then-couple made waves on the red carpet.

▲Accompanied by her mother, actress Blythe Danner, Paltrow made her red carpet debut in 1991 at the premiere of 'Prince of Tides.'

▲The pre–Michelle Williams Destiny's Child walked their first red carpet at the 12th annual Soul Train Music Awards in 1998. Beyoncé is beaming beside Kelly Rowland, LeToya Luckett, and LaTavia Roberson.

▲In 1997, the actors released 'Good Will Hunting,' which launched them into Hollywood with several Oscars, including one for Best Screenplay. Minnie Driver (middle) also got a Best Supporting Actress nom.

▲Six years before becoming the 'Twilight' star, the actress was still a girl and appeared at the 2002 premiere of 'Panic Room.'

▲In 2001, at the age of 11, the actress made her red carpet debut with the first 'Harry Potter' film.

▲The singer was just 16 when she made her first appearance at the 2006 CMT Music Awards with that curly blonde hair.

▲Before becoming the heartthrob he is today, Gosling made his Hollywood debut with 2001's 'The Believer.'

▲One year before the 1999 release of '...Baby One More Time,' Spears walked the red carpet of the American Music Awards at the tender age of 16.

▲The bubbly blonde radiated charisma and beauty in this Gucci outfit at the 1998 MTV Music Awards.

▲Before the ponytails, spray tans, and much higher boots, the singer and actress walked the red carpet for the premiere of Broadway musical '13' in 2008.

▲The actress made her film and red carpet debut in 1999 with the release of 'Drop Dead Gorgeous.'

▲A snapshot of the first appearance of one of the world's most famous families: Khloé, Kourtney, Kim, Rob, pre-transition Caitlyn Jenner, and Kris Jenner attended the premiere of 'Cinderella' in 1995.

▲In 1996, two years before she would strike gold with 'The Mask of Zorro,' Catherine Zeta-Jones stepped out for the premiere of 'The Long Kiss Goodnight.'

▲Long before 'Pitch Perfect,' Anna Kendrick stepped out in 2003 for the premiere of the film 'Camp' during the IFP Los Angeles Film Festival.

▲Blake Lively is now well-known for her contemporary style, but in 2005 she stepped out in ripped wide-leg jeans, a pink statement belt, and heels for the Kids' Choice Awards.

▲In 2006, before all the twists and turns of her career, Cyrus accompanied her father to the Annual Academy Of Country Music Awards.

▲Post-'Barney' and pre-'Wizards of Waverly Place,' Gomez made her red carpet debut at the premiere of Walt Disney's 'Pirates Of The Caribbean: At World's End' in May 2007.

▲The singer made a statement in 2008, at her first red carpet for Chevy, with zebra-print leggings under a dress and a flower-pinned mini-blazer.

▲Back in 2008, the actress rocked a tutu-type skirt at the premiere party for NBC's 'My Own Worst Enemy.'

▲The young actress made her red carpet debut at the premiere of 'The Princess Diaries 2: Royal Engagement' in 2004.

▲Pictured with Rob Williams at the 2004 Step-Up Women's Network's Fashion Forward Luncheon, the singer was still known as Katy Hudson, and her hit album 'One of the Boys' wouldn't come out for another four years.

▲In 2001, long before she hit her stride, Washington wore a cheesy New York tourist shirt at her first red carpet for the premiere of 'Save the Last Dance.'

▲She's still so young and only increasing in popularity, but Zendaya made her first red carpet appearance at Disney and ABC's Television Critics Association party in 2010.

▲Hilton might've been born into fame, but she still took time adjusting. She wore sunglasses and a white dress with long fringe for her first red carpet at a PlayStation 2 event in 2000.

▲Pratt was not always the heartthrob he is now. He's pictured in 2003 at the People's Choice Awards.

▲Cameron Diaz and her now-ex-boyfriend had their 1997 red carpet debut at the premiere of 'In & Out.'

▲Though not her first-ever red carpet appearance, this 1997 red carpet marked her big year of coming out, first on television and then in public appearances with then-partner Anne Heche.

▲Before lip fillers and bad brand endorsements, the young TV personalities coordinated outfits at KIIS-FM's 2008 Wango Tango concert.

▲In 2013, four years before 'Call Me By Your Name,' and before he raised the bar for men's fashion, the young actor attended the Entertainment Weekly Pre-SAG Party.

▲'Superbad' co-stars Jonah Hill and Emma Stone are pictured at Teen Vogue's Young Hollywood party in 2006, a year before the film's release.

▲Long before she was an Oscar winner, J-Law walked her first red carpet at the Movieguide Faith & Values Awards in 2007.

▲Long before 'Jane the Virgin,' the actress attended the Los Angeles Latino International Film Festival opening gala in 2011.

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Though her red carpet debut was in 1994, she managed to look even younger in 1995, at the 'Things You Do in Denver' premiere.

▲J-Lo is pictured here four years before the release of her album 'On The 6,' with Wesley Snipes and Woody Harrelson at the 'Money Train' premiere in 1995.

▲The young pop princess is pictured at the 1999 Billboard Awards, the same year she dropped her debut album 'So Real.'

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When you've been following polished celebrities' careers for a long time, it's easy to forget how awkward and young they looked when they first broke into the industry. Some looked completely unprepared for the massive international fame that would eventually find them, and others just seemed so adorably naive and innocent.

Click through to see your favorite stars' first appearances in the big leagues, and see who's made the biggest transformations.